Hard to tell, isn't it?
The Culkin Dynasty began with Home Alone (1990), a Christmas movie about a young boy (10-year old Macaulay Culkin) accidentally left at home when his family goes away for the holidays. The top film of the year, and the top-grossing live comedy of all time, it propelled Macaulay into child superstardom.
He grew up thin, pretty, and androgynous -- everyone assumed that he was gay -- with a heavy-lidded, world-weary, knowing expression that actors often use to denote depravity.
Who knew that there was a whole family of Culkins back home, including four boys who would all grow up thin, pretty, and androgynous, with the trademark world-weary, knowing expression. I keep assuming that they're gay, and going to their movies, expecting them to play gay characters. But they almost never do.
1. Macaulay (born 1980). No gay characters, but his Michael Alig identifies as gay in Party Monster (#6 on my list of the 10 Gay Movies I Hated). He's more of an anything-for-a-thrill decadent who almost Finds True Love with a girl. Macaulay also played a handicapped decadent youth in Saved (2004), which has a gay character.
There's a sausage sighting story about Mac on Tales of West Hollywood.
2. Kieran (born 1982). After a small part in Home Alone, he established himself as a talented actor, specializing in quirky indie movies like The Dangerous Lives of Altar Boys (which sounds like it is gay-themed, but isn't) and Igby Goes Down (which sounds gay themed, but isn't; I walked out after seeing the homophobic portrayal of a bi drug dealer). Kieran also played the world-weary, knowing gay roommate in Scott Pilgrim vs. the World (2010).
3. Shane, born 1986. Not into acting.
4. Christian, born 1987. Not into acting, though he played Kieran's brother in It Runs in the Family (1994).
5. Rory, born 1989. He's grabbing up all of the quirky indie movies that Kieran turns down, such as Mean Creek (which is about bullying but has no gay characters) and Chumscrubber (which I keep getting mixed up with the gay-themed Borstal Boy). In The Night Listener (2006), his character, who bonds with gay radio host Gabriel Noone (Robin Williams), should be gay but isn't.
Answer: Rory.